# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email spfe@sogang.ac.kr _publ_contact_author_name 'In-chul ' loop_ _publ_author_name 'N. Ahmed' 'I.C. Hwang' 'Kwang Kim' data_1-TBA-CH3CO2 _database_code_depnum_ccdc_archive 'CCDC 820422' #TrackingRef '4931_web_deposit_cif_file_0_In-chulHwang_1301988714.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; "Cyclo-bis-(urea-3,6-dichlorocarbazole)[TBA-acetate]" ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 N,0.5(C26 H14 Cl4 N6 O2),C2 H3 O2' _chemical_formula_sum 'C62 H90 Cl4 N8 O6' _chemical_formula_weight 1185.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8875(11) _cell_length_b 13.7511(17) _cell_length_c 15.0665(19) _cell_angle_alpha 64.753(2) _cell_angle_beta 77.356(3) _cell_angle_gamma 74.412(2) _cell_volume 1592.6(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 652 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 19.72 _exptl_crystal_description stick _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area dector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8908 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.70 _reflns_number_total 5938 _reflns_number_gt 3418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SainT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0873P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5938 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1184 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.2103 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.03926(14) 0.89023(8) 1.20236(9) 0.0925(4) Uani 1 1 d . . . Cl2 Cl 0.59260(18) 1.06277(8) 0.67313(10) 0.1162(5) Uani 1 1 d . . . O1 O 0.6920(2) 0.52752(17) 0.95223(18) 0.0527(6) Uani 1 1 d . . . N1 N 0.4092(3) 0.6620(2) 0.9748(2) 0.0503(7) Uani 1 1 d . . . H1 H 0.4374 0.5942 0.9828 0.060 Uiso 1 1 calc R . . N2 N 0.6458(3) 0.6501(2) 0.7956(2) 0.0505(7) Uani 1 1 d . . . H2 H 0.6540 0.6573 0.7352 0.061 Uiso 1 1 calc R . . N3 N 0.7573(3) 0.4712(2) 0.8232(2) 0.0547(7) Uani 1 1 d . . . H3N H 0.7797 0.4959 0.7599 0.066 Uiso 1 1 calc R . . C1 C 0.2983(4) 0.7012(2) 1.0360(3) 0.0488(8) Uani 1 1 d . . . C2 C 0.2827(4) 0.8158(2) 0.9997(3) 0.0526(9) Uani 1 1 d . . . C3 C 0.1783(4) 0.8760(3) 1.0502(3) 0.0632(10) Uani 1 1 d . . . H3 H 0.1670 0.9518 1.0268 0.076 Uiso 1 1 calc R . . C4 C 0.0930(4) 0.8195(3) 1.1358(3) 0.0606(10) Uani 1 1 d . . . C5 C 0.4698(4) 0.7465(2) 0.8985(3) 0.0481(8) Uani 1 1 d . . . C6 C 0.3938(4) 0.8448(3) 0.9110(3) 0.0544(9) Uani 1 1 d . . . C7 C 0.4327(4) 0.9443(3) 0.8408(3) 0.0643(10) Uani 1 1 d . . . H7 H 0.3859 1.0102 0.8478 0.077 Uiso 1 1 calc R . . C8 C 0.5402(5) 0.9415(3) 0.7625(3) 0.0655(10) Uani 1 1 d . . . C9 C 0.6138(4) 0.8442(3) 0.7483(3) 0.0601(9) Uani 1 1 d . . . H9 H 0.6858 0.8471 0.6926 0.072 Uiso 1 1 calc R . . C10 C 0.5803(4) 0.7442(2) 0.8164(3) 0.0482(8) Uani 1 1 d . . . C11 C 0.6973(4) 0.5480(3) 0.8638(3) 0.0472(8) Uani 1 1 d . . . C12 C 0.2136(4) 0.6437(2) 1.1265(3) 0.0493(8) Uani 1 1 d . . . C13 C 0.1099(4) 0.7055(3) 1.1740(3) 0.0572(9) Uani 1 1 d . . . H13 H 0.0500 0.6707 1.2328 0.069 Uiso 1 1 calc R . . N4 N 0.8066(3) 0.3365(2) 0.2911(2) 0.0530(7) Uani 1 1 d . . . C14 C 0.6905(4) 0.4415(3) 0.2436(3) 0.0568(9) Uani 1 1 d . . . H14A H 0.5928 0.4401 0.2877 0.068 Uiso 1 1 calc R . . H14B H 0.6684 0.4422 0.1831 0.068 Uiso 1 1 calc R . . C15 C 0.7424(4) 0.5478(3) 0.2192(3) 0.0645(10) Uani 1 1 d . . . H15A H 0.7469 0.5549 0.2799 0.077 Uiso 1 1 calc R . . H15B H 0.8469 0.5465 0.1827 0.077 Uiso 1 1 calc R . . C16 C 0.6283(4) 0.6451(3) 0.1580(3) 0.0693(11) Uani 1 1 d . . . H16A H 0.5217 0.6369 0.1878 0.083 Uiso 1 1 calc R . . H16B H 0.6405 0.6455 0.0923 0.083 Uiso 1 1 calc R . . C17 C 0.6526(5) 0.7551(3) 0.1492(3) 0.0870(13) Uani 1 1 d . . . H17A H 0.6385 0.7560 0.2139 0.131 Uiso 1 1 calc R . . H17B H 0.5774 0.8136 0.1100 0.131 Uiso 1 1 calc R . . H17C H 0.7571 0.7647 0.1183 0.131 Uiso 1 1 calc R . . C18 C 0.8554(4) 0.3354(3) 0.3812(3) 0.0598(9) Uani 1 1 d . . . H18A H 0.9095 0.3955 0.3604 0.072 Uiso 1 1 calc R . . H18B H 0.9303 0.2677 0.4092 0.072 Uiso 1 1 calc R . . C19 C 0.7236(4) 0.3447(3) 0.4618(3) 0.0685(10) Uani 1 1 d . . . H19A H 0.6559 0.4165 0.4375 0.082 Uiso 1 1 calc R . . H19B H 0.6610 0.2902 0.4778 0.082 Uiso 1 1 calc R . . C20 C 0.7838(5) 0.3285(3) 0.5534(3) 0.0777(12) Uani 1 1 d . . . H20A H 0.8534 0.3791 0.5361 0.093 Uiso 1 1 calc R . . H20B H 0.8449 0.2546 0.5803 0.093 Uiso 1 1 calc R . . C21 C 0.6547(5) 0.3462(4) 0.6314(3) 0.0926(14) Uani 1 1 d . . . H21A H 0.5974 0.4205 0.6065 0.139 Uiso 1 1 calc R . . H21B H 0.6996 0.3324 0.6890 0.139 Uiso 1 1 calc R . . H21C H 0.5847 0.2969 0.6483 0.139 Uiso 1 1 calc R . . C22 C 0.7243(4) 0.2417(3) 0.3191(3) 0.0577(9) Uani 1 1 d . . . H22A H 0.6241 0.2552 0.3576 0.069 Uiso 1 1 calc R . . H22B H 0.7023 0.2414 0.2589 0.069 Uiso 1 1 calc R . . C23 C 0.8143(4) 0.1287(3) 0.3774(3) 0.0727(11) Uani 1 1 d . . . H23A H 0.9147 0.1141 0.3395 0.087 Uiso 1 1 calc R . . H23B H 0.8352 0.1275 0.4385 0.087 Uiso 1 1 calc R . . C24 C 0.7263(5) 0.0413(3) 0.4008(4) 0.0883(14) Uani 1 1 d . . . H24A H 0.7067 0.0423 0.3396 0.106 Uiso 1 1 calc R . . H24B H 0.6252 0.0570 0.4376 0.106 Uiso 1 1 calc R . . C25 C 0.8125(6) -0.0721(3) 0.4604(4) 0.1133(18) Uani 1 1 d . . . H25A H 0.9106 -0.0897 0.4232 0.170 Uiso 1 1 calc R . . H25B H 0.7492 -0.1248 0.4746 0.170 Uiso 1 1 calc R . . H25C H 0.8323 -0.0738 0.5212 0.170 Uiso 1 1 calc R . . C26 C 0.9535(4) 0.3266(3) 0.2191(3) 0.0602(9) Uani 1 1 d . . . H26A H 1.0111 0.3816 0.2099 0.072 Uiso 1 1 calc R . . H26B H 1.0197 0.2553 0.2494 0.072 Uiso 1 1 calc R . . C27 C 1.0691(4) 0.2889(3) 0.0663(3) 0.0762(12) Uani 1 1 d . . . H27A H 1.1612 0.3110 0.0706 0.091 Uiso 1 1 calc R . . H27B H 1.0554 0.3172 -0.0030 0.091 Uiso 1 1 calc R . . C28 C 0.9280(4) 0.3392(4) 0.1188(3) 0.0790(12) Uani 1 1 d . . . H28A H 0.8405 0.3055 0.1265 0.095 Uiso 1 1 calc R . . H28B H 0.8993 0.4167 0.0782 0.095 Uiso 1 1 calc R . . C29 C 1.0977(6) 0.1650(4) 0.1076(4) 0.1054(16) Uani 1 1 d . . . H29A H 1.1010 0.1365 0.1776 0.158 Uiso 1 1 calc R . . H29B H 1.1961 0.1374 0.0766 0.158 Uiso 1 1 calc R . . H29C H 1.0141 0.1425 0.0948 0.158 Uiso 1 1 calc R . . C30 C 0.2404(4) 0.3807(3) 0.4276(3) 0.0592(9) Uani 1 1 d . . . C31 C 0.2238(5) 0.3587(3) 0.5359(3) 0.0800(12) Uani 1 1 d . . . H31A H 0.3147 0.3722 0.5501 0.120 Uiso 1 1 calc R . . H31B H 0.2148 0.2837 0.5746 0.120 Uiso 1 1 calc R . . H31C H 0.1313 0.4063 0.5520 0.120 Uiso 1 1 calc R . . O2 O 0.1413(3) 0.4557(2) 0.3757(2) 0.0746(8) Uani 1 1 d . . . O3 O 0.3530(3) 0.3239(2) 0.3950(2) 0.0810(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1050(8) 0.0666(7) 0.0940(9) -0.0436(6) 0.0116(7) 0.0035(6) Cl2 0.1551(12) 0.0505(6) 0.1115(11) -0.0169(6) 0.0300(9) -0.0326(7) O1 0.0574(14) 0.0463(13) 0.0548(15) -0.0185(12) -0.0148(12) -0.0069(10) N1 0.0530(16) 0.0363(14) 0.0607(18) -0.0192(14) -0.0064(14) -0.0075(12) N2 0.0559(16) 0.0416(15) 0.0523(17) -0.0187(14) -0.0049(14) -0.0079(12) N3 0.0602(17) 0.0417(15) 0.0550(18) -0.0169(14) -0.0029(14) -0.0054(13) C1 0.0477(19) 0.0431(18) 0.059(2) -0.0239(17) -0.0131(17) -0.0025(14) C2 0.057(2) 0.0417(18) 0.060(2) -0.0215(17) -0.0145(18) -0.0023(15) C3 0.073(2) 0.0405(19) 0.071(3) -0.0220(19) -0.015(2) 0.0019(17) C4 0.062(2) 0.049(2) 0.068(3) -0.0273(19) -0.009(2) 0.0029(17) C5 0.0518(19) 0.0370(17) 0.057(2) -0.0169(16) -0.0163(17) -0.0060(14) C6 0.057(2) 0.0439(19) 0.062(2) -0.0186(17) -0.0160(18) -0.0060(15) C7 0.072(2) 0.0400(19) 0.078(3) -0.0229(19) -0.011(2) -0.0052(17) C8 0.080(3) 0.0399(19) 0.069(3) -0.0142(18) -0.011(2) -0.0105(18) C9 0.064(2) 0.048(2) 0.062(2) -0.0131(18) -0.0075(19) -0.0131(17) C10 0.0458(18) 0.0447(18) 0.054(2) -0.0194(16) -0.0094(16) -0.0062(14) C11 0.0403(17) 0.0446(19) 0.058(2) -0.0193(18) -0.0060(16) -0.0123(14) C12 0.0468(18) 0.0447(18) 0.056(2) -0.0201(17) -0.0113(16) -0.0030(14) C13 0.056(2) 0.055(2) 0.057(2) -0.0217(18) -0.0065(18) -0.0061(16) N4 0.0438(15) 0.0594(17) 0.0539(18) -0.0188(14) -0.0094(14) -0.0102(13) C14 0.0456(19) 0.061(2) 0.062(2) -0.0219(19) -0.0124(17) -0.0071(16) C15 0.063(2) 0.064(2) 0.066(3) -0.022(2) -0.013(2) -0.0135(18) C16 0.069(2) 0.067(2) 0.067(3) -0.025(2) -0.013(2) -0.0042(19) C17 0.100(3) 0.064(3) 0.092(3) -0.031(2) -0.009(3) -0.010(2) C18 0.055(2) 0.063(2) 0.061(2) -0.0207(19) -0.0156(19) -0.0102(17) C19 0.068(2) 0.081(3) 0.062(2) -0.031(2) -0.006(2) -0.019(2) C20 0.078(3) 0.090(3) 0.071(3) -0.037(2) -0.015(2) -0.011(2) C21 0.089(3) 0.128(4) 0.080(3) -0.055(3) -0.001(3) -0.034(3) C22 0.053(2) 0.060(2) 0.063(2) -0.0240(19) -0.0063(18) -0.0171(17) C23 0.066(2) 0.061(2) 0.080(3) -0.016(2) -0.008(2) -0.0151(19) C24 0.104(3) 0.070(3) 0.098(4) -0.029(3) -0.027(3) -0.022(2) C25 0.149(5) 0.057(3) 0.119(4) -0.024(3) -0.013(4) -0.018(3) C26 0.048(2) 0.070(2) 0.060(2) -0.024(2) -0.0051(18) -0.0109(17) C27 0.069(3) 0.102(3) 0.066(3) -0.039(3) -0.004(2) -0.021(2) C28 0.064(3) 0.103(3) 0.059(3) -0.025(2) -0.009(2) -0.010(2) C29 0.135(4) 0.087(3) 0.108(4) -0.045(3) -0.030(4) -0.021(3) C30 0.057(2) 0.061(2) 0.060(2) -0.025(2) 0.006(2) -0.0210(18) C31 0.084(3) 0.088(3) 0.065(3) -0.033(2) -0.005(2) -0.014(2) O2 0.0732(17) 0.0727(17) 0.0667(18) -0.0245(15) -0.0005(15) -0.0077(14) O3 0.0760(18) 0.0899(19) 0.0639(18) -0.0325(16) -0.0052(15) 0.0058(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.743(4) . ? Cl2 C8 1.743(4) . ? O1 C11 1.232(4) . ? N1 C1 1.361(4) . ? N1 C5 1.374(4) . ? N1 H1 0.8600 . ? N2 C11 1.366(4) . ? N2 C10 1.405(4) . ? N2 H2 0.8600 . ? N3 C11 1.371(4) . ? N3 C12 1.408(4) 2_667 ? N3 H3N 0.8600 . ? C1 C2 1.408(4) . ? C1 C12 1.415(5) . ? C2 C3 1.394(5) . ? C2 C6 1.450(5) . ? C3 C4 1.369(5) . ? C3 H3 0.9300 . ? C4 C13 1.397(4) . ? C5 C10 1.406(5) . ? C5 C6 1.412(4) . ? C6 C7 1.403(4) . ? C7 C8 1.354(5) . ? C7 H7 0.9300 . ? C8 C9 1.405(5) . ? C9 C10 1.384(4) . ? C9 H9 0.9300 . ? C12 C13 1.376(4) . ? C12 N3 1.408(4) 2_667 ? C13 H13 0.9300 . ? N4 C18 1.507(4) . ? N4 C14 1.518(4) . ? N4 C26 1.520(4) . ? N4 C22 1.522(4) . ? C14 C15 1.522(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.515(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.531(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.513(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.496(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.503(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.517(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.485(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.513(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C28 1.507(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.498(5) . ? C27 C29 1.512(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 O3 1.243(4) . ? C30 O2 1.255(4) . ? C30 C31 1.508(5) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C5 110.2(3) . . ? C1 N1 H1 124.9 . . ? C5 N1 H1 124.9 . . ? C11 N2 C10 125.0(3) . . ? C11 N2 H2 117.5 . . ? C10 N2 H2 117.5 . . ? C11 N3 C12 127.2(3) . 2_667 ? C11 N3 H3N 116.4 . . ? C12 N3 H3N 116.4 2_667 . ? N1 C1 C2 109.1(3) . . ? N1 C1 C12 129.7(3) . . ? C2 C1 C12 121.0(3) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 C6 133.4(3) . . ? C1 C2 C6 105.9(3) . . ? C4 C3 C2 117.5(3) . . ? C4 C3 H3 121.3 . . ? C2 C3 H3 121.3 . . ? C3 C4 C13 122.6(3) . . ? C3 C4 Cl1 119.6(3) . . ? C13 C4 Cl1 117.8(3) . . ? N1 C5 C10 129.4(3) . . ? N1 C5 C6 107.9(3) . . ? C10 C5 C6 122.5(3) . . ? C7 C6 C5 119.2(3) . . ? C7 C6 C2 134.0(3) . . ? C5 C6 C2 106.8(3) . . ? C8 C7 C6 118.0(3) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C9 123.2(3) . . ? C7 C8 Cl2 119.8(3) . . ? C9 C8 Cl2 117.0(3) . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 N2 119.0(3) . . ? C9 C10 C5 116.4(3) . . ? N2 C10 C5 124.3(3) . . ? O1 C11 N2 123.5(3) . . ? O1 C11 N3 123.6(3) . . ? N2 C11 N3 112.9(3) . . ? C13 C12 N3 117.9(3) . 2_667 ? C13 C12 C1 117.0(3) . . ? N3 C12 C1 124.5(3) 2_667 . ? C12 C13 C4 121.3(3) . . ? C12 C13 H13 119.4 . . ? C4 C13 H13 119.4 . . ? C18 N4 C14 110.5(3) . . ? C18 N4 C26 108.1(2) . . ? C14 N4 C26 110.5(3) . . ? C18 N4 C22 110.7(3) . . ? C14 N4 C22 107.0(2) . . ? C26 N4 C22 110.0(3) . . ? N4 C14 C15 116.0(3) . . ? N4 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N4 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 110.3(3) . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 113.0(3) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C18 C19 115.7(3) . . ? N4 C18 H18A 108.3 . . ? C19 C18 H18A 108.3 . . ? N4 C18 H18B 108.3 . . ? C19 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C20 C19 C18 112.2(3) . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 113.0(3) . . ? C19 C20 H20A 109.0 . . ? C21 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 N4 115.7(3) . . ? C23 C22 H22A 108.4 . . ? N4 C22 H22A 108.4 . . ? C23 C22 H22B 108.4 . . ? N4 C22 H22B 108.4 . . ? H22A C22 H22B 107.4 . . ? C24 C23 C22 112.1(3) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 C24 C25 113.2(4) . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24B 108.9 . . ? C25 C24 H24B 108.9 . . ? H24A C24 H24B 107.8 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C28 C26 N4 116.4(3) . . ? C28 C26 H26A 108.2 . . ? N4 C26 H26A 108.2 . . ? C28 C26 H26B 108.2 . . ? N4 C26 H26B 108.2 . . ? H26A C26 H26B 107.3 . . ? C28 C27 C29 113.5(4) . . ? C28 C27 H27A 108.9 . . ? C29 C27 H27A 108.9 . . ? C28 C27 H27B 108.9 . . ? C29 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C27 C28 C26 113.6(3) . . ? C27 C28 H28A 108.8 . . ? C26 C28 H28A 108.8 . . ? C27 C28 H28B 108.8 . . ? C26 C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O3 C30 O2 124.0(4) . . ? O3 C30 C31 117.7(4) . . ? O2 C30 C31 118.3(4) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 0.3(4) . . . . ? C5 N1 C1 C12 -175.3(3) . . . . ? N1 C1 C2 C3 -178.7(3) . . . . ? C12 C1 C2 C3 -2.6(5) . . . . ? N1 C1 C2 C6 -0.3(4) . . . . ? C12 C1 C2 C6 175.8(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C6 C2 C3 C4 -177.7(4) . . . . ? C2 C3 C4 C13 1.5(6) . . . . ? C2 C3 C4 Cl1 179.9(3) . . . . ? C1 N1 C5 C10 -176.5(3) . . . . ? C1 N1 C5 C6 -0.2(4) . . . . ? N1 C5 C6 C7 -178.6(3) . . . . ? C10 C5 C6 C7 -1.9(5) . . . . ? N1 C5 C6 C2 0.0(4) . . . . ? C10 C5 C6 C2 176.7(3) . . . . ? C3 C2 C6 C7 -3.4(7) . . . . ? C1 C2 C6 C7 178.5(4) . . . . ? C3 C2 C6 C5 178.3(4) . . . . ? C1 C2 C6 C5 0.2(4) . . . . ? C5 C6 C7 C8 1.2(5) . . . . ? C2 C6 C7 C8 -176.9(4) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? C6 C7 C8 Cl2 180.0(3) . . . . ? C7 C8 C9 C10 -1.0(6) . . . . ? Cl2 C8 C9 C10 179.2(3) . . . . ? C8 C9 C10 N2 174.5(3) . . . . ? C8 C9 C10 C5 0.3(5) . . . . ? C11 N2 C10 C9 143.2(3) . . . . ? C11 N2 C10 C5 -43.0(5) . . . . ? N1 C5 C10 C9 177.0(3) . . . . ? C6 C5 C10 C9 1.1(5) . . . . ? N1 C5 C10 N2 3.2(5) . . . . ? C6 C5 C10 N2 -172.8(3) . . . . ? C10 N2 C11 O1 -0.2(5) . . . . ? C10 N2 C11 N3 -179.4(3) . . . . ? C12 N3 C11 O1 16.5(5) 2_667 . . . ? C12 N3 C11 N2 -164.3(3) 2_667 . . . ? N1 C1 C12 C13 178.5(3) . . . . ? C2 C1 C12 C13 3.4(5) . . . . ? N1 C1 C12 N3 7.2(5) . . . 2_667 ? C2 C1 C12 N3 -168.0(3) . . . 2_667 ? N3 C12 C13 C4 170.2(3) 2_667 . . . ? C1 C12 C13 C4 -1.8(5) . . . . ? C3 C4 C13 C12 -0.6(6) . . . . ? Cl1 C4 C13 C12 -179.1(3) . . . . ? C18 N4 C14 C15 53.4(4) . . . . ? C26 N4 C14 C15 -66.3(4) . . . . ? C22 N4 C14 C15 174.0(3) . . . . ? N4 C14 C15 C16 171.0(3) . . . . ? C14 C15 C16 C17 167.8(3) . . . . ? C14 N4 C18 C19 58.8(4) . . . . ? C26 N4 C18 C19 179.9(3) . . . . ? C22 N4 C18 C19 -59.5(4) . . . . ? N4 C18 C19 C20 172.7(3) . . . . ? C18 C19 C20 C21 175.5(4) . . . . ? C18 N4 C22 C23 -53.6(4) . . . . ? C14 N4 C22 C23 -174.0(3) . . . . ? C26 N4 C22 C23 65.8(4) . . . . ? N4 C22 C23 C24 -179.6(3) . . . . ? C22 C23 C24 C25 -179.1(4) . . . . ? C18 N4 C26 C28 -173.2(3) . . . . ? C14 N4 C26 C28 -52.1(4) . . . . ? C22 N4 C26 C28 65.9(4) . . . . ? C29 C27 C28 C26 74.5(5) . . . . ? N4 C26 C28 C27 -158.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.70 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.318 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.071 data_1-TBA-Cl _database_code_depnum_ccdc_archive 'CCDC 820423' #TrackingRef '4931_web_deposit_cif_file_0_In-chulHwang_1301988714.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; "Cyclo-bis-(urea-3,6-dichlorocarbazole)2[(n-Bu)4NCl]" ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H36 N),C26 H14 Cl4 N6 O2,2(Cl)' _chemical_formula_sum 'C58 H86 Cl6 N8 O2' _chemical_formula_weight 1140.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.644(3) _cell_length_b 15.163(3) _cell_length_c 16.546(4) _cell_angle_alpha 84.368(4) _cell_angle_beta 78.777(4) _cell_angle_gamma 72.600(4) _cell_volume 3201.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 658 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 24.81 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16799 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.1130 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 25.11 _reflns_number_total 11123 _reflns_number_gt 3481 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1193P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11123 _refine_ls_number_parameters 675 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2370 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2824 _refine_ls_wR_factor_gt 0.1903 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2329(5) 0.8245(4) 0.3712(5) 0.0766(17) Uani 1 1 d . . . C2 C -0.1949(6) 0.8135(4) 0.4456(5) 0.0785(17) Uani 1 1 d . . . C3 C -0.2680(6) 0.8299(4) 0.5163(4) 0.0875(19) Uani 1 1 d . . . H3 H -0.2462 0.8228 0.5671 0.105 Uiso 1 1 calc R . . C4 C -0.3743(6) 0.8569(5) 0.5134(5) 0.098(2) Uani 1 1 d . . . C5 C -0.4141(5) 0.8672(4) 0.4432(5) 0.100(2) Uani 1 1 d . . . H5 H -0.4855 0.8841 0.4435 0.120 Uiso 1 1 calc R . . C6 C -0.3406(5) 0.8509(4) 0.3692(5) 0.0842(18) Uani 1 1 d . . . C7 C -0.3513(5) 0.8512(4) 0.2840(5) 0.0844(19) Uani 1 1 d . . . C8 C -0.4364(5) 0.8663(5) 0.2454(5) 0.100(2) Uani 1 1 d . . . H8 H -0.5040 0.8822 0.2752 0.120 Uiso 1 1 calc R . . C9 C -0.4179(5) 0.8571(5) 0.1622(6) 0.097(2) Uani 1 1 d . . . C10 C -0.3179(6) 0.8336(4) 0.1153(4) 0.0900(19) Uani 1 1 d . . . H10 H -0.3091 0.8290 0.0586 0.108 Uiso 1 1 calc R . . C11 C -0.2317(5) 0.8172(4) 0.1528(5) 0.0786(18) Uani 1 1 d . . . C12 C -0.2501(5) 0.8266(4) 0.2386(4) 0.0757(17) Uani 1 1 d . . . C13 C -0.0403(5) 0.7966(5) 0.1158(4) 0.0779(17) Uani 1 1 d . . . C14 C 0.1870(5) 0.7304(4) 0.1455(5) 0.0783(17) Uani 1 1 d . . . C15 C 0.1501(5) 0.7327(4) 0.0700(5) 0.0803(18) Uani 1 1 d . . . C16 C 0.2229(6) 0.7134(4) -0.0003(5) 0.093(2) Uani 1 1 d . . . H16 H 0.2009 0.7140 -0.0502 0.112 Uiso 1 1 calc R . . C17 C 0.3282(7) 0.6929(5) 0.0008(5) 0.104(2) Uani 1 1 d . . . C18 C 0.3652(5) 0.6908(5) 0.0735(6) 0.104(2) Uani 1 1 d . . . H18 H 0.4365 0.6762 0.0730 0.125 Uiso 1 1 calc R . . C19 C 0.2950(5) 0.7107(4) 0.1472(5) 0.089(2) Uani 1 1 d . . . C20 C 0.3055(6) 0.7111(4) 0.2315(5) 0.0866(19) Uani 1 1 d . . . C21 C 0.3913(5) 0.6947(5) 0.2716(6) 0.105(2) Uani 1 1 d . . . H21 H 0.4590 0.6822 0.2421 0.127 Uiso 1 1 calc R . . C22 C 0.3717(6) 0.6979(5) 0.3548(6) 0.105(2) Uani 1 1 d . . . C23 C 0.2714(6) 0.7136(4) 0.4015(5) 0.098(2) Uani 1 1 d . . . H23 H 0.2625 0.7123 0.4587 0.117 Uiso 1 1 calc R . . C24 C 0.1853(5) 0.7311(4) 0.3637(5) 0.0805(18) Uani 1 1 d . . . C25 C 0.2040(5) 0.7293(4) 0.2782(5) 0.0833(18) Uani 1 1 d . . . C26 C -0.0065(5) 0.7925(5) 0.3961(5) 0.0768(18) Uani 1 1 d . . . C27 C 0.9189(7) 0.4720(5) 0.2347(5) 0.132(3) Uani 1 1 d . . . H27A H 0.9420 0.4351 0.2823 0.158 Uiso 1 1 calc R . . H27B H 0.9345 0.4302 0.1901 0.158 Uiso 1 1 calc R . . C28 C 0.9846(11) 0.5376(8) 0.2101(7) 0.225(6) Uani 1 1 d . . . H28A H 0.9662 0.5844 0.2508 0.270 Uiso 1 1 calc R . . H28B H 0.9720 0.5684 0.1573 0.270 Uiso 1 1 calc R . . C29 C 1.1027(12) 0.4819(14) 0.2038(10) 0.305(12) Uani 1 1 d . . . H29A H 1.1053 0.4174 0.2025 0.366 Uiso 1 1 calc R . . H29B H 1.1364 0.4983 0.1497 0.366 Uiso 1 1 calc R . . C30 C 1.1559(16) 0.4837(14) 0.2476(12) 0.402(16) Uani 1 1 d . . . H30A H 1.1150 0.5124 0.2972 0.602 Uiso 1 1 calc R . . H30B H 1.2030 0.5184 0.2220 0.602 Uiso 1 1 calc R . . H30C H 1.1951 0.4216 0.2607 0.602 Uiso 1 1 calc R . . C31 C 0.7583(8) 0.5700(6) 0.1840(7) 0.158(3) Uani 1 1 d . . . H31A H 0.7933 0.6178 0.1697 0.190 Uiso 1 1 calc R . . H31B H 0.6848 0.6004 0.2024 0.190 Uiso 1 1 calc R . . C32 C 0.7696(10) 0.5179(8) 0.1059(8) 0.197(5) Uani 1 1 d . . . H32A H 0.7404 0.4662 0.1196 0.237 Uiso 1 1 calc R . . H32B H 0.8427 0.4941 0.0820 0.237 Uiso 1 1 calc R . . C33 C 0.7107(17) 0.5865(13) 0.0440(10) 0.275(10) Uani 1 1 d . . . H33A H 0.6517 0.6288 0.0767 0.330 Uiso 1 1 calc R . . H33B H 0.7568 0.6226 0.0174 0.330 Uiso 1 1 calc R . . C34 C 0.6785(12) 0.5641(12) -0.0081(11) 0.286(10) Uani 1 1 d . . . H34A H 0.7323 0.5165 -0.0383 0.429 Uiso 1 1 calc R . . H34B H 0.6560 0.6164 -0.0447 0.429 Uiso 1 1 calc R . . H34C H 0.6205 0.5409 0.0156 0.429 Uiso 1 1 calc R . . C35 C 0.7572(6) 0.4296(5) 0.2770(5) 0.119(3) Uani 1 1 d . . . H35A H 0.7864 0.3949 0.3235 0.142 Uiso 1 1 calc R . . H35B H 0.7805 0.3893 0.2308 0.142 Uiso 1 1 calc R . . C36 C 0.6381(7) 0.4533(6) 0.2989(6) 0.152(3) Uani 1 1 d . . . H36A H 0.6130 0.4968 0.3427 0.183 Uiso 1 1 calc R . . H36B H 0.6078 0.4825 0.2511 0.183 Uiso 1 1 calc R . . C37 C 0.6039(8) 0.3679(7) 0.3263(7) 0.182(4) Uani 1 1 d . . . H37A H 0.6293 0.3243 0.2825 0.218 Uiso 1 1 calc R . . H37B H 0.6342 0.3387 0.3740 0.218 Uiso 1 1 calc R . . C38 C 0.4907(10) 0.3898(9) 0.3470(9) 0.261(7) Uani 1 1 d . . . H38A H 0.4657 0.4312 0.3917 0.392 Uiso 1 1 calc R . . H38B H 0.4712 0.3340 0.3632 0.392 Uiso 1 1 calc R . . H38C H 0.4605 0.4188 0.2998 0.392 Uiso 1 1 calc R . . C39 C 0.7735(7) 0.5741(5) 0.3269(6) 0.147(3) Uani 1 1 d . . . H39A H 0.8049 0.6241 0.3106 0.176 Uiso 1 1 calc R . . H39B H 0.6985 0.6012 0.3374 0.176 Uiso 1 1 calc R . . C40 C 0.8070(9) 0.5289(7) 0.4063(6) 0.202(5) Uani 1 1 d . . . H40A H 0.7854 0.4729 0.4178 0.243 Uiso 1 1 calc R . . H40B H 0.8826 0.5108 0.3982 0.243 Uiso 1 1 calc R . . C41 C 0.8057(11) 0.5475(8) 0.5476(8) 0.228(6) Uani 1 1 d . . . H41A H 0.7844 0.4930 0.5666 0.341 Uiso 1 1 calc R . . H41B H 0.7783 0.5928 0.5891 0.341 Uiso 1 1 calc R . . H41C H 0.8804 0.5318 0.5371 0.341 Uiso 1 1 calc R . . C42 C 0.7679(11) 0.5834(8) 0.4756(8) 0.211(5) Uani 1 1 d . . . H42A H 0.7826 0.6424 0.4615 0.253 Uiso 1 1 calc R . . H42B H 0.6927 0.5957 0.4870 0.253 Uiso 1 1 calc R . . Cl1 Cl -0.52085(15) 0.87249(16) 0.10827(15) 0.1416(9) Uani 1 1 d . . . Cl2 Cl 0.41392(17) 0.66738(18) -0.09290(15) 0.1562(9) Uani 1 1 d . . . Cl3 Cl 0.47518(15) 0.68042(16) 0.40690(15) 0.1490(9) Uani 1 1 d . . . Cl4 Cl -0.46112(16) 0.87787(18) 0.60645(14) 0.1520(9) Uani 1 1 d . . . N1 N -0.1785(4) 0.8077(3) 0.2918(4) 0.0782(14) Uani 1 1 d . . . H1 H -0.1118 0.7888 0.2778 0.094 Uiso 1 1 calc R . . N2 N -0.1322(4) 0.7835(3) 0.1046(3) 0.0845(15) Uani 1 1 d . . . H2 H -0.1286 0.7512 0.0636 0.101 Uiso 1 1 calc R . . N3 N 0.0451(4) 0.7436(4) 0.0668(3) 0.0899(16) Uani 1 1 d . . . H3A H 0.0333 0.7137 0.0299 0.108 Uiso 1 1 calc R . . N4 N 0.1339(4) 0.7391(3) 0.2243(4) 0.0832(15) Uani 1 1 d . . . H4 H 0.0676 0.7491 0.2387 0.100 Uiso 1 1 calc R . . N5 N 0.0877(4) 0.7397(3) 0.4137(3) 0.0860(15) Uani 1 1 d . . . H5A H 0.0871 0.7086 0.4601 0.103 Uiso 1 1 calc R . . N6 N -0.0895(4) 0.7788(3) 0.4515(3) 0.0841(15) Uani 1 1 d . . . H6 H -0.0752 0.7450 0.4949 0.101 Uiso 1 1 calc R . . N7 N 0.8015(6) 0.5105(5) 0.2552(4) 0.123(2) Uani 1 1 d . . . O1 O -0.0369(3) 0.8519(3) 0.1653(3) 0.0829(12) Uani 1 1 d . . . O2 O -0.0156(3) 0.8466(3) 0.3359(3) 0.0814(12) Uani 1 1 d . . . C43 C -0.0032(5) 0.1187(4) 0.2404(4) 0.0896(19) Uani 1 1 d . . . H43A H -0.0132 0.1586 0.1913 0.108 Uiso 1 1 calc R . . H43B H -0.0176 0.1583 0.2864 0.108 Uiso 1 1 calc R . . C44 C -0.0834(5) 0.0649(4) 0.2549(4) 0.097(2) Uani 1 1 d . . . H44A H -0.0684 0.0227 0.2108 0.116 Uiso 1 1 calc R . . H44B H -0.0789 0.0286 0.3064 0.116 Uiso 1 1 calc R . . C45 C -0.1910(5) 0.1287(5) 0.2582(6) 0.139(3) Uani 1 1 d . . . H45A H -0.1947 0.1643 0.2063 0.166 Uiso 1 1 calc R . . H45B H -0.2042 0.1718 0.3014 0.166 Uiso 1 1 calc R . . C46 C -0.2754(6) 0.0809(6) 0.2740(6) 0.166(4) Uani 1 1 d . . . H46A H -0.2741 0.0472 0.3263 0.249 Uiso 1 1 calc R . . H46B H -0.2637 0.0388 0.2311 0.249 Uiso 1 1 calc R . . H46C H -0.3420 0.1261 0.2748 0.249 Uiso 1 1 calc R . . C47 C 0.1348(5) -0.0029(5) 0.3040(5) 0.106(2) Uani 1 1 d . . . H47A H 0.0930 -0.0456 0.3102 0.127 Uiso 1 1 calc R . . H47B H 0.2074 -0.0391 0.2916 0.127 Uiso 1 1 calc R . . C48 C 0.1183(6) 0.0390(5) 0.3835(6) 0.128(3) Uani 1 1 d . . . H48A H 0.0446 0.0703 0.3992 0.154 Uiso 1 1 calc R . . H48B H 0.1555 0.0854 0.3769 0.154 Uiso 1 1 calc R . . C49 C 0.1545(6) -0.0310(5) 0.4546(5) 0.124(3) Uani 1 1 d . . . H49A H 0.1228 -0.0013 0.5065 0.149 Uiso 1 1 calc R . . H49B H 0.1273 -0.0831 0.4540 0.149 Uiso 1 1 calc R . . C50 C 0.2675(7) -0.0670(6) 0.4531(7) 0.188(5) Uani 1 1 d . . . H50A H 0.2947 -0.0173 0.4600 0.282 Uiso 1 1 calc R . . H50B H 0.3008 -0.0944 0.4012 0.282 Uiso 1 1 calc R . . H50C H 0.2807 -0.1129 0.4970 0.282 Uiso 1 1 calc R . . C51 C 0.1714(5) 0.1332(4) 0.2163(4) 0.095(2) Uani 1 1 d . . . H51A H 0.1506 0.1743 0.1700 0.114 Uiso 1 1 calc R . . H51B H 0.1518 0.1702 0.2646 0.114 Uiso 1 1 calc R . . C52 C 0.2870(5) 0.0949(5) 0.2000(5) 0.134(3) Uani 1 1 d . . . H52A H 0.3084 0.0559 0.1529 0.161 Uiso 1 1 calc R . . H52B H 0.3102 0.0575 0.2475 0.161 Uiso 1 1 calc R . . C53 C 0.3364(7) 0.1743(7) 0.1827(7) 0.170(4) Uani 1 1 d . . . H53A H 0.3074 0.2152 0.1390 0.204 Uiso 1 1 calc R . . H53B H 0.3201 0.2097 0.2318 0.204 Uiso 1 1 calc R . . C54 C 0.4464(10) 0.1405(9) 0.1591(8) 0.248(6) Uani 1 1 d . . . H54A H 0.4626 0.1029 0.1122 0.373 Uiso 1 1 calc R . . H54B H 0.4758 0.1042 0.2040 0.373 Uiso 1 1 calc R . . H54C H 0.4752 0.1917 0.1450 0.373 Uiso 1 1 calc R . . C55 C 0.1380(5) -0.0010(4) 0.1577(5) 0.097(2) Uani 1 1 d . . . H55A H 0.2116 -0.0342 0.1518 0.117 Uiso 1 1 calc R . . H55B H 0.0995 -0.0464 0.1709 0.117 Uiso 1 1 calc R . . C56 C 0.1168(6) 0.0464(5) 0.0762(5) 0.121(3) Uani 1 1 d . . . H56A H 0.1525 0.0939 0.0639 0.145 Uiso 1 1 calc R . . H56B H 0.0426 0.0768 0.0809 0.145 Uiso 1 1 calc R . . C57 C 0.1518(7) -0.0197(5) 0.0020(6) 0.134(3) Uani 1 1 d . . . H57A H 0.1198 -0.0697 0.0154 0.160 Uiso 1 1 calc R . . H57B H 0.1267 0.0145 -0.0462 0.160 Uiso 1 1 calc R . . C58 C 0.2613(7) -0.0578(6) -0.0174(6) 0.159(3) Uani 1 1 d . . . H58A H 0.2857 -0.0976 0.0278 0.239 Uiso 1 1 calc R . . H58B H 0.2938 -0.0088 -0.0270 0.239 Uiso 1 1 calc R . . H58C H 0.2786 -0.0928 -0.0661 0.239 Uiso 1 1 calc R . . N8 N 0.1098(4) 0.0622(3) 0.2301(3) 0.0858(15) Uani 1 1 d . . . Cl5 Cl 0.94744(16) 0.68613(13) 0.93313(13) 0.1264(8) Uani 1 1 d . . . Cl6 Cl 0.02328(18) 0.70882(13) 0.60448(12) 0.1350(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.070(5) 0.067(4) 0.094(6) -0.021(4) -0.002(4) -0.023(3) C2 0.082(5) 0.077(4) 0.087(5) -0.017(4) -0.021(5) -0.031(4) C3 0.085(5) 0.092(5) 0.090(6) -0.021(4) -0.013(4) -0.028(4) C4 0.093(6) 0.110(5) 0.093(6) -0.025(4) 0.004(5) -0.038(4) C5 0.080(5) 0.101(5) 0.114(7) -0.021(5) 0.003(5) -0.027(4) C6 0.079(5) 0.083(4) 0.099(6) -0.013(4) -0.022(5) -0.030(4) C7 0.055(4) 0.080(4) 0.121(7) -0.016(4) -0.017(4) -0.019(3) C8 0.078(5) 0.101(5) 0.127(7) -0.021(5) -0.024(5) -0.027(4) C9 0.065(5) 0.101(5) 0.138(7) -0.012(5) -0.041(5) -0.027(4) C10 0.089(5) 0.084(5) 0.107(6) 0.002(4) -0.039(5) -0.029(4) C11 0.064(4) 0.071(4) 0.104(6) -0.014(4) -0.015(4) -0.021(3) C12 0.075(5) 0.068(4) 0.090(5) -0.010(4) -0.020(4) -0.023(3) C13 0.081(5) 0.072(4) 0.083(5) 0.009(4) -0.022(4) -0.024(4) C14 0.067(5) 0.076(4) 0.094(6) -0.018(4) -0.003(4) -0.026(3) C15 0.077(5) 0.069(4) 0.097(6) -0.014(4) -0.013(5) -0.022(3) C16 0.093(5) 0.092(5) 0.098(6) -0.017(4) -0.006(5) -0.034(4) C17 0.097(6) 0.110(6) 0.102(6) -0.024(5) 0.014(5) -0.038(4) C18 0.077(5) 0.097(5) 0.143(8) -0.023(5) -0.011(6) -0.035(4) C19 0.062(5) 0.083(5) 0.118(7) -0.024(4) 0.012(5) -0.025(3) C20 0.080(5) 0.079(4) 0.099(6) -0.021(4) -0.013(5) -0.017(4) C21 0.071(5) 0.105(5) 0.147(8) -0.030(5) -0.040(5) -0.015(4) C22 0.080(6) 0.107(6) 0.136(7) -0.030(5) -0.046(6) -0.014(4) C23 0.080(5) 0.086(5) 0.128(6) -0.012(4) -0.042(5) -0.008(4) C24 0.073(5) 0.072(4) 0.094(6) -0.010(4) -0.020(5) -0.012(3) C25 0.064(5) 0.076(4) 0.112(6) -0.012(4) -0.014(5) -0.023(3) C26 0.076(5) 0.075(5) 0.094(6) -0.022(4) -0.025(5) -0.030(4) C27 0.151(8) 0.102(6) 0.138(8) -0.031(5) -0.004(6) -0.033(6) C28 0.287(16) 0.187(11) 0.219(13) -0.077(9) 0.068(12) -0.145(12) C29 0.184(13) 0.47(3) 0.31(2) -0.23(2) 0.089(14) -0.196(17) C30 0.55(4) 0.32(2) 0.43(3) -0.012(19) -0.37(3) -0.08(2) C31 0.208(10) 0.106(7) 0.156(9) 0.002(7) -0.041(8) -0.035(6) C32 0.273(14) 0.163(10) 0.170(11) 0.046(9) -0.076(10) -0.076(9) C33 0.44(3) 0.299(19) 0.199(15) 0.084(14) -0.159(16) -0.23(2) C34 0.182(12) 0.30(2) 0.34(3) 0.114(18) -0.080(16) -0.032(13) C35 0.157(8) 0.071(5) 0.120(7) 0.001(4) -0.014(5) -0.030(5) C36 0.119(7) 0.135(8) 0.177(9) -0.023(7) -0.003(6) -0.009(6) C37 0.151(9) 0.131(8) 0.252(13) -0.028(8) 0.012(9) -0.046(7) C38 0.187(13) 0.235(14) 0.36(2) -0.038(13) -0.007(13) -0.073(11) C39 0.173(8) 0.100(6) 0.144(8) -0.051(6) 0.009(7) -0.014(5) C40 0.292(14) 0.146(9) 0.114(8) -0.051(7) -0.025(9) 0.027(9) C41 0.338(19) 0.193(12) 0.161(12) -0.045(10) -0.067(12) -0.063(11) C42 0.291(16) 0.163(10) 0.173(12) -0.042(10) -0.039(12) -0.045(10) Cl1 0.0986(14) 0.170(2) 0.170(2) -0.0209(16) -0.0602(14) -0.0328(13) Cl2 0.1201(17) 0.205(2) 0.145(2) -0.0512(18) 0.0235(14) -0.0639(16) Cl3 0.0892(14) 0.176(2) 0.183(2) -0.0558(17) -0.0581(14) -0.0037(13) Cl4 0.1171(16) 0.199(2) 0.1288(19) -0.0425(17) 0.0229(14) -0.0458(15) N1 0.061(3) 0.077(3) 0.097(4) -0.018(3) -0.020(3) -0.011(2) N2 0.082(4) 0.094(4) 0.091(4) -0.014(3) -0.030(3) -0.032(3) N3 0.079(4) 0.102(4) 0.097(4) -0.028(3) -0.013(3) -0.032(3) N4 0.063(3) 0.094(4) 0.100(5) -0.014(3) -0.017(4) -0.027(3) N5 0.080(4) 0.084(4) 0.096(4) 0.000(3) -0.026(4) -0.021(3) N6 0.081(4) 0.091(4) 0.086(4) 0.001(3) -0.022(3) -0.031(3) N7 0.146(6) 0.087(5) 0.119(6) -0.006(4) -0.009(5) -0.013(4) O1 0.085(3) 0.077(3) 0.094(3) -0.014(2) -0.024(2) -0.028(2) O2 0.081(3) 0.073(3) 0.098(3) -0.007(3) -0.023(3) -0.028(2) C43 0.083(5) 0.074(4) 0.110(5) -0.021(4) -0.012(4) -0.017(4) C44 0.076(5) 0.088(5) 0.129(6) -0.017(4) -0.018(4) -0.023(4) C45 0.083(5) 0.116(6) 0.210(10) -0.029(6) -0.010(5) -0.021(5) C46 0.089(6) 0.161(8) 0.245(12) -0.017(7) 0.000(6) -0.048(6) C47 0.116(6) 0.094(5) 0.120(7) 0.003(5) -0.027(5) -0.049(4) C48 0.149(7) 0.107(6) 0.143(8) -0.016(6) -0.023(6) -0.056(5) C49 0.138(7) 0.093(6) 0.143(8) 0.003(5) -0.039(6) -0.030(5) C50 0.140(8) 0.132(8) 0.303(15) -0.041(8) -0.063(9) -0.031(6) C51 0.109(5) 0.083(5) 0.110(6) 0.001(4) -0.020(4) -0.054(4) C52 0.094(6) 0.141(7) 0.185(9) -0.013(6) -0.001(5) -0.073(5) C53 0.104(7) 0.203(10) 0.231(11) -0.001(8) -0.018(7) -0.095(7) C54 0.245(15) 0.249(14) 0.299(17) -0.005(12) -0.022(13) -0.160(13) C55 0.093(5) 0.078(5) 0.119(6) -0.018(5) -0.004(4) -0.027(4) C56 0.135(6) 0.106(6) 0.123(7) -0.040(6) 0.004(6) -0.042(5) C57 0.135(7) 0.097(6) 0.170(9) -0.022(6) -0.026(6) -0.029(5) C58 0.146(8) 0.131(8) 0.198(10) -0.031(7) -0.009(7) -0.043(6) N8 0.086(4) 0.071(3) 0.105(4) -0.008(3) -0.013(3) -0.031(3) Cl5 0.1457(17) 0.1194(15) 0.1199(16) -0.0392(12) -0.0406(13) -0.0250(12) Cl6 0.173(2) 0.1090(15) 0.0987(15) -0.0220(12) -0.0361(14) 0.0090(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.384(7) . ? C1 C2 1.403(8) . ? C1 C6 1.408(8) . ? C2 C3 1.370(8) . ? C2 N6 1.395(7) . ? C3 C4 1.394(8) . ? C3 H3 0.9300 . ? C4 C5 1.352(9) . ? C4 Cl4 1.742(7) . ? C5 C6 1.414(9) . ? C5 H5 0.9300 . ? C6 C7 1.444(9) . ? C7 C8 1.383(8) . ? C7 C12 1.397(8) . ? C8 C9 1.365(9) . ? C8 H8 0.9300 . ? C9 C10 1.394(9) . ? C9 Cl1 1.753(6) . ? C10 C11 1.382(7) . ? C10 H10 0.9300 . ? C11 C12 1.406(8) . ? C11 N2 1.408(7) . ? C12 N1 1.390(7) . ? C13 O1 1.244(7) . ? C13 N3 1.364(7) . ? C13 N2 1.376(7) . ? C14 N4 1.361(7) . ? C14 C19 1.419(8) . ? C14 C15 1.428(8) . ? C15 C16 1.367(8) . ? C15 N3 1.403(7) . ? C16 C17 1.380(9) . ? C16 H16 0.9300 . ? C17 C18 1.385(9) . ? C17 Cl2 1.750(7) . ? C18 C19 1.394(9) . ? C18 H18 0.9300 . ? C19 C20 1.429(9) . ? C20 C21 1.403(8) . ? C20 C25 1.411(8) . ? C21 C22 1.353(9) . ? C21 H21 0.9300 . ? C22 C23 1.399(9) . ? C22 Cl3 1.735(7) . ? C23 C24 1.382(8) . ? C23 H23 0.9300 . ? C24 C25 1.389(8) . ? C24 N5 1.401(8) . ? C25 N4 1.398(7) . ? C26 O2 1.228(7) . ? C26 N5 1.365(7) . ? C26 N6 1.365(8) . ? C27 C28 1.507(12) . ? C27 N7 1.513(9) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.567(18) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.128(16) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 N7 1.514(10) . ? C31 C32 1.538(12) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.545(17) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.160(18) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 N7 1.507(8) . ? C35 C36 1.532(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.505(11) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.458(12) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 C40 1.507(11) . ? C39 N7 1.521(9) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C42 1.402(12) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? C41 C42 1.388(12) . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? N1 H1 0.8600 . ? N2 H2 0.8600 . ? N3 H3A 0.8600 . ? N4 H4 0.8600 . ? N5 H5A 0.8600 . ? N6 H6 0.8600 . ? C43 N8 1.509(7) . ? C43 C44 1.521(7) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.491(8) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.505(9) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 C48 1.465(9) . ? C47 N8 1.520(8) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 C49 1.556(10) . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 C50 1.470(10) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 C52 1.489(8) . ? C51 N8 1.528(7) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 C53 1.525(10) . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C54 1.421(13) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 H54A 0.9600 . ? C54 H54B 0.9600 . ? C54 H54C 0.9600 . ? C55 C56 1.502(9) . ? C55 N8 1.526(7) . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C56 C57 1.571(9) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C57 C58 1.414(9) . ? C57 H57A 0.9700 . ? C57 H57B 0.9700 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 129.3(6) . . ? N1 C1 C6 108.8(6) . . ? C2 C1 C6 121.8(7) . . ? C3 C2 N6 119.3(6) . . ? C3 C2 C1 116.6(6) . . ? N6 C2 C1 123.8(6) . . ? C2 C3 C4 121.1(6) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 124.2(7) . . ? C5 C4 Cl4 118.1(6) . . ? C3 C4 Cl4 117.7(7) . . ? C4 C5 C6 116.0(7) . . ? C4 C5 H5 122.0 . . ? C6 C5 H5 122.0 . . ? C1 C6 C5 120.4(7) . . ? C1 C6 C7 106.9(6) . . ? C5 C6 C7 132.6(7) . . ? C8 C7 C12 120.5(7) . . ? C8 C7 C6 133.1(7) . . ? C12 C7 C6 106.4(6) . . ? C9 C8 C7 117.7(7) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C8 C9 C10 122.9(6) . . ? C8 C9 Cl1 121.0(6) . . ? C10 C9 Cl1 116.1(7) . . ? C11 C10 C9 120.3(7) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 117.1(6) . . ? C10 C11 N2 118.1(7) . . ? C12 C11 N2 124.5(6) . . ? N1 C12 C7 109.6(6) . . ? N1 C12 C11 128.8(6) . . ? C7 C12 C11 121.5(6) . . ? O1 C13 N3 124.2(6) . . ? O1 C13 N2 122.8(6) . . ? N3 C13 N2 113.0(6) . . ? N4 C14 C19 108.6(6) . . ? N4 C14 C15 130.0(6) . . ? C19 C14 C15 121.3(7) . . ? C16 C15 N3 119.3(7) . . ? C16 C15 C14 117.5(6) . . ? N3 C15 C14 122.8(6) . . ? C15 C16 C17 121.7(7) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C16 C17 C18 121.5(7) . . ? C16 C17 Cl2 117.5(7) . . ? C18 C17 Cl2 121.0(7) . . ? C17 C18 C19 119.7(7) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C14 118.3(8) . . ? C18 C19 C20 134.4(7) . . ? C14 C19 C20 107.2(6) . . ? C21 C20 C25 119.7(7) . . ? C21 C20 C19 133.7(7) . . ? C25 C20 C19 106.5(6) . . ? C22 C21 C20 117.4(7) . . ? C22 C21 H21 121.3 . . ? C20 C21 H21 121.3 . . ? C21 C22 C23 123.0(7) . . ? C21 C22 Cl3 119.0(7) . . ? C23 C22 Cl3 117.9(7) . . ? C24 C23 C22 120.9(7) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 116.8(7) . . ? C23 C24 N5 118.3(7) . . ? C25 C24 N5 124.6(6) . . ? C24 C25 N4 129.4(6) . . ? C24 C25 C20 122.2(7) . . ? N4 C25 C20 108.3(7) . . ? O2 C26 N5 123.1(7) . . ? O2 C26 N6 123.3(7) . . ? N5 C26 N6 113.5(7) . . ? C28 C27 N7 119.4(8) . . ? C28 C27 H27A 107.5 . . ? N7 C27 H27A 107.5 . . ? C28 C27 H27B 107.5 . . ? N7 C27 H27B 107.5 . . ? H27A C27 H27B 107.0 . . ? C27 C28 C29 109.2(11) . . ? C27 C28 H28A 109.8 . . ? C29 C28 H28A 109.8 . . ? C27 C28 H28B 109.8 . . ? C29 C28 H28B 109.8 . . ? H28A C28 H28B 108.3 . . ? C30 C29 C28 126.6(18) . . ? C30 C29 H29A 105.7 . . ? C28 C29 H29A 105.7 . . ? C30 C29 H29B 105.7 . . ? C28 C29 H29B 105.7 . . ? H29A C29 H29B 106.1 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N7 C31 C32 115.1(7) . . ? N7 C31 H31A 108.5 . . ? C32 C31 H31A 108.5 . . ? N7 C31 H31B 108.5 . . ? C32 C31 H31B 108.5 . . ? H31A C31 H31B 107.5 . . ? C31 C32 C33 108.0(11) . . ? C31 C32 H32A 110.1 . . ? C33 C32 H32A 110.1 . . ? C31 C32 H32B 110.1 . . ? C33 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? C34 C33 C32 124(2) . . ? C34 C33 H33A 106.4 . . ? C32 C33 H33A 106.4 . . ? C34 C33 H33B 106.4 . . ? C32 C33 H33B 106.4 . . ? H33A C33 H33B 106.4 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N7 C35 C36 116.1(6) . . ? N7 C35 H35A 108.3 . . ? C36 C35 H35A 108.3 . . ? N7 C35 H35B 108.3 . . ? C36 C35 H35B 108.3 . . ? H35A C35 H35B 107.4 . . ? C37 C36 C35 111.1(7) . . ? C37 C36 H36A 109.4 . . ? C35 C36 H36A 109.4 . . ? C37 C36 H36B 109.4 . . ? C35 C36 H36B 109.4 . . ? H36A C36 H36B 108.0 . . ? C38 C37 C36 111.4(9) . . ? C38 C37 H37A 109.3 . . ? C36 C37 H37A 109.3 . . ? C38 C37 H37B 109.3 . . ? C36 C37 H37B 109.3 . . ? H37A C37 H37B 108.0 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 N7 115.5(7) . . ? C40 C39 H39A 108.4 . . ? N7 C39 H39A 108.4 . . ? C40 C39 H39B 108.4 . . ? N7 C39 H39B 108.4 . . ? H39A C39 H39B 107.5 . . ? C42 C40 C39 115.6(9) . . ? C42 C40 H40A 108.4 . . ? C39 C40 H40A 108.4 . . ? C42 C40 H40B 108.4 . . ? C39 C40 H40B 108.4 . . ? H40A C40 H40B 107.4 . . ? C42 C41 H41A 109.5 . . ? C42 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C42 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C41 C42 C40 117.0(12) . . ? C41 C42 H42A 108.1 . . ? C40 C42 H42A 108.1 . . ? C41 C42 H42B 108.1 . . ? C40 C42 H42B 108.1 . . ? H42A C42 H42B 107.3 . . ? C1 N1 C12 108.3(5) . . ? C1 N1 H1 125.9 . . ? C12 N1 H1 125.9 . . ? C13 N2 C11 127.1(5) . . ? C13 N2 H2 116.4 . . ? C11 N2 H2 116.4 . . ? C13 N3 C15 127.1(5) . . ? C13 N3 H3A 116.5 . . ? C15 N3 H3A 116.5 . . ? C14 N4 C25 109.3(5) . . ? C14 N4 H4 125.3 . . ? C25 N4 H4 125.3 . . ? C26 N5 C24 126.4(6) . . ? C26 N5 H5A 116.8 . . ? C24 N5 H5A 116.8 . . ? C26 N6 C2 127.3(6) . . ? C26 N6 H6 116.3 . . ? C2 N6 H6 116.3 . . ? C35 N7 C27 107.5(6) . . ? C35 N7 C31 111.9(7) . . ? C27 N7 C31 111.2(7) . . ? C35 N7 C39 111.3(6) . . ? C27 N7 C39 109.1(7) . . ? C31 N7 C39 105.9(7) . . ? N8 C43 C44 116.5(5) . . ? N8 C43 H43A 108.2 . . ? C44 C43 H43A 108.2 . . ? N8 C43 H43B 108.2 . . ? C44 C43 H43B 108.2 . . ? H43A C43 H43B 107.3 . . ? C45 C44 C43 110.9(5) . . ? C45 C44 H44A 109.5 . . ? C43 C44 H44A 109.5 . . ? C45 C44 H44B 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 108.0 . . ? C44 C45 C46 114.2(7) . . ? C44 C45 H45A 108.7 . . ? C46 C45 H45A 108.7 . . ? C44 C45 H45B 108.7 . . ? C46 C45 H45B 108.7 . . ? H45A C45 H45B 107.6 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C48 C47 N8 117.2(6) . . ? C48 C47 H47A 108.0 . . ? N8 C47 H47A 108.0 . . ? C48 C47 H47B 108.0 . . ? N8 C47 H47B 108.0 . . ? H47A C47 H47B 107.2 . . ? C47 C48 C49 114.3(7) . . ? C47 C48 H48A 108.7 . . ? C49 C48 H48A 108.7 . . ? C47 C48 H48B 108.7 . . ? C49 C48 H48B 108.7 . . ? H48A C48 H48B 107.6 . . ? C50 C49 C48 116.8(8) . . ? C50 C49 H49A 108.1 . . ? C48 C49 H49A 108.1 . . ? C50 C49 H49B 108.1 . . ? C48 C49 H49B 108.1 . . ? H49A C49 H49B 107.3 . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C52 C51 N8 115.9(5) . . ? C52 C51 H51A 108.3 . . ? N8 C51 H51A 108.3 . . ? C52 C51 H51B 108.3 . . ? N8 C51 H51B 108.3 . . ? H51A C51 H51B 107.4 . . ? C51 C52 C53 109.4(6) . . ? C51 C52 H52A 109.8 . . ? C53 C52 H52A 109.8 . . ? C51 C52 H52B 109.8 . . ? C53 C52 H52B 109.8 . . ? H52A C52 H52B 108.2 . . ? C54 C53 C52 111.0(9) . . ? C54 C53 H53A 109.4 . . ? C52 C53 H53A 109.4 . . ? C54 C53 H53B 109.4 . . ? C52 C53 H53B 109.4 . . ? H53A C53 H53B 108.0 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C56 C55 N8 115.6(6) . . ? C56 C55 H55A 108.4 . . ? N8 C55 H55A 108.4 . . ? C56 C55 H55B 108.4 . . ? N8 C55 H55B 108.4 . . ? H55A C55 H55B 107.4 . . ? C55 C56 C57 114.5(7) . . ? C55 C56 H56A 108.6 . . ? C57 C56 H56A 108.6 . . ? C55 C56 H56B 108.6 . . ? C57 C56 H56B 108.6 . . ? H56A C56 H56B 107.6 . . ? C58 C57 C56 113.0(7) . . ? C58 C57 H57A 109.0 . . ? C56 C57 H57A 109.0 . . ? C58 C57 H57B 109.0 . . ? C56 C57 H57B 109.0 . . ? H57A C57 H57B 107.8 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C43 N8 C47 112.9(5) . . ? C43 N8 C55 110.9(5) . . ? C47 N8 C55 104.6(5) . . ? C43 N8 C51 105.1(4) . . ? C47 N8 C51 111.7(5) . . ? C55 N8 C51 111.9(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -175.7(5) . . . . ? C6 C1 C2 C3 0.0(8) . . . . ? N1 C1 C2 N6 -2.3(9) . . . . ? C6 C1 C2 N6 173.4(5) . . . . ? N6 C2 C3 C4 -174.4(5) . . . . ? C1 C2 C3 C4 -0.6(9) . . . . ? C2 C3 C4 C5 1.4(10) . . . . ? C2 C3 C4 Cl4 -178.9(5) . . . . ? C3 C4 C5 C6 -1.4(10) . . . . ? Cl4 C4 C5 C6 179.0(5) . . . . ? N1 C1 C6 C5 176.5(5) . . . . ? C2 C1 C6 C5 0.0(9) . . . . ? N1 C1 C6 C7 -0.9(6) . . . . ? C2 C1 C6 C7 -177.3(5) . . . . ? C4 C5 C6 C1 0.7(9) . . . . ? C4 C5 C6 C7 177.2(6) . . . . ? C1 C6 C7 C8 175.9(6) . . . . ? C5 C6 C7 C8 -1.0(12) . . . . ? C1 C6 C7 C12 -0.9(6) . . . . ? C5 C6 C7 C12 -177.8(6) . . . . ? C12 C7 C8 C9 -0.6(9) . . . . ? C6 C7 C8 C9 -177.0(7) . . . . ? C7 C8 C9 C10 -0.2(10) . . . . ? C7 C8 C9 Cl1 178.7(5) . . . . ? C8 C9 C10 C11 0.9(10) . . . . ? Cl1 C9 C10 C11 -178.0(4) . . . . ? C9 C10 C11 C12 -0.9(8) . . . . ? C9 C10 C11 N2 172.8(5) . . . . ? C8 C7 C12 N1 -174.9(5) . . . . ? C6 C7 C12 N1 2.4(6) . . . . ? C8 C7 C12 C11 0.6(9) . . . . ? C6 C7 C12 C11 177.9(5) . . . . ? C10 C11 C12 N1 174.7(5) . . . . ? N2 C11 C12 N1 1.4(9) . . . . ? C10 C11 C12 C7 0.1(8) . . . . ? N2 C11 C12 C7 -173.1(5) . . . . ? N4 C14 C15 C16 -174.0(6) . . . . ? C19 C14 C15 C16 1.3(9) . . . . ? N4 C14 C15 N3 -1.2(10) . . . . ? C19 C14 C15 N3 174.1(5) . . . . ? N3 C15 C16 C17 -173.4(6) . . . . ? C14 C15 C16 C17 -0.4(9) . . . . ? C15 C16 C17 C18 0.1(10) . . . . ? C15 C16 C17 Cl2 178.9(5) . . . . ? C16 C17 C18 C19 -0.7(10) . . . . ? Cl2 C17 C18 C19 -179.5(5) . . . . ? C17 C18 C19 C14 1.5(10) . . . . ? C17 C18 C19 C20 176.8(7) . . . . ? N4 C14 C19 C18 174.3(5) . . . . ? C15 C14 C19 C18 -1.9(9) . . . . ? N4 C14 C19 C20 -2.1(7) . . . . ? C15 C14 C19 C20 -178.3(5) . . . . ? C18 C19 C20 C21 2.8(13) . . . . ? C14 C19 C20 C21 178.4(6) . . . . ? C18 C19 C20 C25 -174.6(7) . . . . ? C14 C19 C20 C25 1.0(7) . . . . ? C25 C20 C21 C22 -0.4(9) . . . . ? C19 C20 C21 C22 -177.6(7) . . . . ? C20 C21 C22 C23 2.1(11) . . . . ? C20 C21 C22 Cl3 -178.7(5) . . . . ? C21 C22 C23 C24 -2.9(11) . . . . ? Cl3 C22 C23 C24 177.8(5) . . . . ? C22 C23 C24 C25 1.9(9) . . . . ? C22 C23 C24 N5 175.5(6) . . . . ? C23 C24 C25 N4 176.0(5) . . . . ? N5 C24 C25 N4 2.9(10) . . . . ? C23 C24 C25 C20 -0.3(9) . . . . ? N5 C24 C25 C20 -173.4(5) . . . . ? C21 C20 C25 C24 -0.5(9) . . . . ? C19 C20 C25 C24 177.4(6) . . . . ? C21 C20 C25 N4 -177.5(5) . . . . ? C19 C20 C25 N4 0.4(7) . . . . ? N7 C27 C28 C29 172.5(9) . . . . ? C27 C28 C29 C30 -109(3) . . . . ? N7 C31 C32 C33 173.6(10) . . . . ? C31 C32 C33 C34 -156(2) . . . . ? N7 C35 C36 C37 -175.3(8) . . . . ? C35 C36 C37 C38 -179.9(10) . . . . ? N7 C39 C40 C42 -170.7(10) . . . . ? C39 C40 C42 C41 -173.6(12) . . . . ? C2 C1 N1 C12 178.5(5) . . . . ? C6 C1 N1 C12 2.3(6) . . . . ? C7 C12 N1 C1 -3.0(6) . . . . ? C11 C12 N1 C1 -178.1(6) . . . . ? O1 C13 N2 C11 -10.1(9) . . . . ? N3 C13 N2 C11 170.5(5) . . . . ? C10 C11 N2 C13 151.8(5) . . . . ? C12 C11 N2 C13 -35.0(9) . . . . ? O1 C13 N3 C15 8.5(10) . . . . ? N2 C13 N3 C15 -172.0(5) . . . . ? C16 C15 N3 C13 -151.5(6) . . . . ? C14 C15 N3 C13 35.9(9) . . . . ? C19 C14 N4 C25 2.4(6) . . . . ? C15 C14 N4 C25 178.2(6) . . . . ? C24 C25 N4 C14 -178.4(6) . . . . ? C20 C25 N4 C14 -1.7(6) . . . . ? O2 C26 N5 C24 -7.1(9) . . . . ? N6 C26 N5 C24 172.4(5) . . . . ? C23 C24 N5 C26 150.0(6) . . . . ? C25 C24 N5 C26 -37.0(9) . . . . ? O2 C26 N6 C2 7.7(9) . . . . ? N5 C26 N6 C2 -171.8(5) . . . . ? C3 C2 N6 C26 -151.0(6) . . . . ? C1 C2 N6 C26 35.7(8) . . . . ? C36 C35 N7 C27 -179.2(7) . . . . ? C36 C35 N7 C31 -56.8(9) . . . . ? C36 C35 N7 C39 61.4(9) . . . . ? C28 C27 N7 C35 179.9(8) . . . . ? C28 C27 N7 C31 57.0(11) . . . . ? C28 C27 N7 C39 -59.4(11) . . . . ? C32 C31 N7 C35 -53.7(11) . . . . ? C32 C31 N7 C27 66.5(11) . . . . ? C32 C31 N7 C39 -175.2(9) . . . . ? C40 C39 N7 C35 56.9(11) . . . . ? C40 C39 N7 C27 -61.6(11) . . . . ? C40 C39 N7 C31 178.7(9) . . . . ? N8 C43 C44 C45 -176.2(6) . . . . ? C43 C44 C45 C46 -178.9(7) . . . . ? N8 C47 C48 C49 -175.0(6) . . . . ? C47 C48 C49 C50 74.3(9) . . . . ? N8 C51 C52 C53 176.8(7) . . . . ? C51 C52 C53 C54 -174.3(9) . . . . ? N8 C55 C56 C57 177.1(5) . . . . ? C55 C56 C57 C58 -66.6(9) . . . . ? C44 C43 N8 C47 -58.3(7) . . . . ? C44 C43 N8 C55 58.7(7) . . . . ? C44 C43 N8 C51 179.8(6) . . . . ? C48 C47 N8 C43 -61.1(7) . . . . ? C48 C47 N8 C55 178.3(6) . . . . ? C48 C47 N8 C51 57.0(8) . . . . ? C56 C55 N8 C43 55.9(7) . . . . ? C56 C55 N8 C47 177.9(6) . . . . ? C56 C55 N8 C51 -61.0(7) . . . . ? C52 C51 N8 C43 -177.0(6) . . . . ? C52 C51 N8 C47 60.3(8) . . . . ? C52 C51 N8 C55 -56.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.286 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.065 # END